Drift Engineering and the Controversial Crisis of Caring

In a previous job, I didn’t find myself solving many problems. At least, not problems that I felt had weight and importance.

Hi, I’m Ryan, and I’m a software engineer who cares about solving problems, and I recently joined Drift.

The hidden pain

Everything seemed right. We were solving difficult technical challenges. We had a team that had fun and cared about each other. The company’s mission and motivation were absolutely philanthropic. So why wasn’t I happy working there?

It all may have just been bad timing: my role, the company’s position in the market, the work I was given, and the direction of the organization were all the result of timing. I was unhappy nonetheless.

Eventually, I expressed that I wanted to try being closer to the customer. Unfortunately, after being given the chance, I made a slip of the tongue with one. I lost access to customers. Even indirect access through our Customer Success team. I felt like I couldn’t pursue what I was most curious about.

Uncovering my unhappiness

To me, the rest of the company felt like a black box that spat out tickets that we resolved (by shipping code, changing a customer config, etc.). I was not fulfilled. There was almost a year of this:

Manager: “Ryan, why aren’t you happy here?”

RB: “I want to be closer to the customer. I want to feel their pains, and empathize with them. I want to build SICK solutions and ship!”

There it was. I wanted to feel my impact. Unfortunately, I wasn’t always this articulate. It took me a while of exploration to understand this was the root of my unhappiness. Afterwards, though, this conversation happened with several folks:

“But can you give any specific project that would be exciting for you? We really want you to stay with us, and we recognize that the best way to do that is to put you on a project you’ll care about.”

“Yes! Put me on X project.”

“Ok! Right after Y is delivered…”

Unfortunately, X never happened. Y kept getting in the way, other things were consistently more important. And while there seemed to be a new Y every time another one was finished, I couldn’t find a higher priority X to take the place of the one I identified.

I recognized that while the company wanted to keep me there, they didn’t have the opportunity I so eagerly desired.

We talked about my desire to deliver real solutions, have ownership over my projects, care deeply about the product and about the customers’ needs and problems. I wanted to use all that to fuel my drive.

I left.

I took those key points above straight into my conversation with Elias (CTO and Co-founder of Drift) when I met with him. Halfway through the conversation he pulled out his phone and started scrolling.

When I was done saying what I wanted in a role and company culture, he handed me the phone. He told me to scroll through the slides from a presentation he gave the company earlier that day.

The focal point for the entire presentation was based around providing the exact opportunity I desired so badly.

He had convinced me that I wanted to come in to meet the team.

On the frontline

The Drift team is small. There’s no place to hide from the customer. As an employee, you need to feel the impact of your efforts. To an engineer, the easiest way is to hop on a chat rotation, or sit in on a customer success call. At Drift, I feel a much stronger feedback loop of my work.

I felt trusted on the first day when Stipe told me to ship code to production.

I felt ownership when Luke mentioned “our app” in passing.

I felt close to the customer when I jumped on a sales call with Ally, and shadowed a chat duty with Pete.

Though I’ve been here a short time, it seems like at Drift, we need everybody at full speed and facing the customer. A difficult challenge, but well worth the work.

Interested in hearing about it? Talk to me! Or — talk to the expert who is growing our team.